As highlighted in a previous post – Hiring salespeople is hard for a few reasons:

  • Even mediocre salespeople are really good at selling themselves
  • Salespeople are a product of their environment – just because they were effective at selling software for X company with all of the resources that X company provided, doesn’t mean they will be effective in your startup environment
  • Great salespeople are always in demand
  • Great salespeople that are successful and making good money have a really hard time leaving those jobs
To select top performing sales people, I follow this 7-step process:
  1. Pre-screen survey
  2. Phone screen
  3. Resume review interview (in person)
  4. Behavioral based interview (in person)
  5. Shadow / ride-day
  6. In-depth reference check & background check
  7. Job fit/personality assessment 
1. Pre-screen survey
None of us have time to review every applicant that applies.  If you’ve got proper exposure to your job and you’ve done an effective job of “selling” the opportunity, you are going to get ample candidates.  Use a short survey to weed out the folks that are definitely not going to be a fit.  I use about 10 t/f questions that are scored so that I can stack rank my applicants and spend time reviewing folks that have a better fit potential.
2. Phone screen
Quick, direct, to the point, 10 – 15 minutes.  Purpose of this is to understand if it warrants an in-person sit down with the candidate.  What do they want to do.  What type of company do they want to work with.  What have they done in the past that would lend them to be successful at your company.  What is their compensation expectation.  Give some further color to the role and the organization.  Find a way to put scored factors down and give them a grade vs. pure gut feel.

3. Resume review interview (in person)
Purpose here is to dive into their past experience. Review each role, successes, failures, how they ranked with the team, why they left, etc.  Alway preface the conversation with, “we do in-depth reference checks and always talk to managers of past roles – just wanted to make you aware of that.” This way you know you are getting an accurate story. 
Score it!
If you are impressed = SELL THEM

4. Behavioral based interview (in person)
Tell me about a time when…  Give me an example of…  Have them tell you stories about past experiences.  This conversation will help you better understand how this person reacts to certain situations and how they will react in your environment. 
Score it!
If you are impressed = SELL THEM

5. Shadow / ride-day
An often overlooked and extremely critical step.  Put them in your environment and have them sell for you.  Our inside sales candidates spend a half hour on the phone calling real prospects.  We give them a list to dial and a script to use.  I’m looking to see 1. if they seem hesitant to start dialing and 2. how do they sound on the phone.
Score it!
If you are impressed = SELL

6. In-depth reference check & background check
We use an automated online tool for reference checks called Skill Survey.  If you’ve got to pick up the phone and call manually so be it.  Don’t make the hire unless you get feedback from all of their past managers.

7. Job fit/personality assessment
Just do it.  We use Caliper.  Don’t trust just what they are telling you.  Match the results of an assessment to what you heard in the interview.  They should match up and tell the same story. 

Other points to note:

*Get multiple people involved
*Stick to the process
*Hire fast – run this process efficiently and speed up if needed – don’t sway from the steps however
*Use data/objectiveness as much as possible
*Request past W2’s to understand what they made – especially for experienced AE hires
*Get a system of record to track the process – I’d recommend Hireology😉
*Hire ahead of plan – plan for some turnover and hire before you need them

The odds are heavily stacked against us when scaling a startup.  Getting the right people on the bus is the first step.

Can I get a Do-Over? My 5 Biggest Sales Mistakes


There is nothing more exhilarating for a startup than closing deals.  Hitting sales targets, beating competitors, and disrupting a market is what drives us. 

I’ve had the incomparable experience of helping grow a sales organization from the ground up.  In 3 years we grew the business from 1 to 40 sales team members and grew our customer base from 20 to almost 2,000.  In that time I’ve made a number of mistakes that were extremely detrimental to the business.  In hindsight, I should have seen what was transpiring.  I should have gotten additional insight from advisors.  I should have read more.  I should have pulled my head out of the weeds.  I didn’t do those things however, and the result was the joy of failure.  I learned a great deal from these mistakes and they will undoubtedly stick with me.

Here are my 5 biggest mistakes that could have changed the outcome of our business:

1. Hiring Bodies

We grew fast and needed to hire a large number of inside sales reps.  We didn’t have a recruiter and we had numbers to hit.  I settled.  I hired people that didn’t blow me away.  I hired bodies, not superstars.  Guess what?  They turned-over and I had to hire all over again.

2. Churn? What Churn?

When I realized that customer churn had become an issue, it was too late.  I was blinded and focused solely on new business and neglected our current customers.  I should have hired someone in a Customer Success or Account Management role much sooner than I did.  I also should have built out a defined process for this area and team.  Because of this, churn took a front seat as our number one challenge for a few excruciating quarters. 

3.  Sales Process and CRM

I spent a few years consulting and building sales process for clients.  I should have known better than to not define our sales process and match that up with the pipeline stages in our CRM.  It wasn’t until we were at about 20 sales people did I really dial in our process.  The outcome of that delay was inconsistent sales behavior and an unorganized CRM.

4.  Discounting

Setting prices low or heavily discounting and thinking that you will be able to increase current customer prices is extremely difficult.  We have gone through a number of pricing iterations.  I regret not pricing our solution based on the value it provides early on.  It took me a long time to be comfortable with walking away from deals. 

5. Define Your Market

Our first target market was small and mid-sized businesses.  Yup, it was that specific!  The spray method didn’t work out too well for us.  We then shifted all of our focus to one, very specific and defined target market.  This shift of focus is one of the biggest attributes to our success. 




The below content was repurposed from Craig Wortmann – sales guru, author, entrepreneur and professor.  Craig believes, and I agree, that we as entrepreneurs and sales people don’t spend enough time working to perfect the art of conversation though we are immersed in it daily.  Here are 3 ways to improve your communication and influence:

1. State the Purpose, Benefit and Check Your Audience

Opening and positioning conversations are critical first steps to communicating with influence.  Providing a Purpose, Benefit, Check on the onset of a conversation can set you up for success.  Here’s an example:

“The purpose of this conversation today is to discuss sales strategies for startup organizations. From this conversation we will gain some insights into how to use sales strategies and improve the sales effectiveness in our startup organizations. How does that sound?” Purpose. Benefit. Check.

You have now gained the other persons buy-in as to why they should be engaged in the call.  They understand the purpose of the conversation and the value they will receive from the time you will spend together.

2. Ask Impact Questions

Asking impact questions is a great way to influence the conversation and drive to the outcome you are hoping for.  Impact questions are more than just closed or open questions as they force a deeper response.  When you get a response of “Hmm.. let me think,” or “good question,” you know you have asked an impact question.

Using impact questions will help you engage in the deeper conversations you need to start building a relationship with your prospects.  A good mix of transactional questions (closed and open) as well as impact questions typically works best.  Too many of one or the other can throw the conversation off track.

3. Don’t Leave a Conversation Without Asking Qualifying Questions

Before we end a sales conversation we must be sure to have asked qualifying questions to help us decide if the opportunity is right.  For example, we need to understand if the timing is right, if they have the budget and if this person has the authority to make the decision.  We can’t afford to invest our time on unqualified sales opportunities.  Here are a few qualifying questions that I find effective:

  • How do you feel about what you just saw?
  • It sounds like you are key in this decision.  Who besides yourself will also be involved?
  • Walk me through the typical decision making process for a project like this.
  • When would the best time be to implement a solution like this?
  • What concerns you most about what you just saw?
  • What would stop you from moving this project forward?
  • What is most important for you personally in this decision?

Qualifying now will save you plenty of time and headaches later.


Craig Wortmann is founder and CEO of Sales Engine, a sales consultancy. He has been a sales person and entrepreneur for more than 20 years and has led three companies. Wortmann is a professor of entrepreneurship at the University of Chicago’s Booth School of Business, where he teaches an award-winning course on entrepreneurial selling as well as other courses. He is also the author of What’s Your Story?, a book about how leaders and sales professionals use stories to connect, engage, and inspire.  You can find his Sales Engine blog here




When you’re a start-up, the one thing you can never get enough of is time. Getting great ideas to market ahead of the competition is what separates the winners from those who wish they won. After all, it’s not just about how great your product or service is, it’s also about who is the first to lock up the market. The winners are the ones who get out there and execute. 

Many entrepreneurs face the challenge of how to catapult sales in spite of limited resources and time. Getting it right can feel daunting, especially to those without sales experience. Getting it wrong is not an option; the stakes are too high, especially when you’re wooing investors.

“Go get 5 marquee clients to sign on and I’m in!” Have you heard something like this from potential investors recently? It’s pretty common.

Investors want assurances that their start-up of choice has what it takes to be successful. Before they’ll commit to the big bucks, they want to see that your great idea has legs and sparks excitement in the market you hope to win.

So what’s an entrepreneur to do? There are 4 main options, each with pros and cons:

  1. The business owner does the selling himself/herself
  2. Hire a top-notch business developer internally
  3. Hire low-level sellers and train them
  4. Outsource part or all of the business development function

The right choice depends on your specific situation. However, when speed to market matters most and you don’t have one more minute in your day, the decision becomes pretty clear.

When I was in this exact situation, I chose #4. Here’s why:

  1. My time was limited and valuable. It was critical for me to spend time only on the activities that no one else could do. For me, that was developing sales strategy, running the high-level prospect meetings and closing deals! Having a senior level business developer pinpoint the right decision makers and initiate new prospect relationships for me was the most efficient and least risky way to capture opportunities.
  2. Internal hire = higher risk
    • Hiring an inexperienced seller looked attractive financially but would have required even more of my time to train and manage with no assurance that it would work.
    • Any new hire (even experienced sellers) can take 2-3 months before he/she is able to go out alone and bring opportunities back. Add another 6-12 months to close a deal plus my time diverted from where I needed to focus and it just didn’t add up.

Outsourcing to a lead generation company was clearly my best option to get new clients on board in less time. Once I had made this decision, it was just a matter of determining what kind of lead generation company was right for me and my business. 

As with most things in life, outsourced sales organizations are not all created equally. If you’re selling coffee to an office manager, almost any lead generation company can help. But when you have big ideas and need a seller who can articulate your vision, only seasoned business developers can do that successfully. I wanted someone who could initiate relationships with high-level decision makers and deliver opportunities to me on a silver platter.

Here’s what I used to measure the sales organizations I considered:

  • Long history of engaging C-suite, SVP and VP level executives – I knew I could potentially fail if they hadn’t been able to do this for others successfully.
  • Senior level business developers – To ensure I was getting top quality sellers, I checked out the careers section of their websites. I wanted to see if they were looking for sellers with 1-2 years’ experience, college grads or “actors with a good voice” kinds of people or mature sellers with 10+ years developing business as well as previously held decision maker roles.
  • Experience the sellers for yourself – I asked to speak to a few of the business developers who would likely be making my calls. I was listening to hear how confident they sounded.
    • How did they make me feel?
    • Did they speak with conviction and sound trustworthy?
    • Did they engage me?
    • How many years of experience did they have calling on high-level decision makers?
    • What was their track record of success?
    • Had they held decision-making roles as well as sales roles?
    • If they were calling me, would I want to hear more?
  • Would they build top-notch sales messaging for me? – You only get one shot to get it right with busy executives, so I knew we needed the right talk track to spark curiosity and secure meetings. I considered:
    • Was it a fill-in-the-blank script or did they have a strategic process in place to get down to the emotional root of why what I had to offer was of extreme value to the prospect?
    • Did they work to develop rock solid answers for objections capable of moving past the objection and securing the meeting?
    • How did they work with me to develop and understand who should be on the A-priority prospect list?

 There are many ways to get to the finish line when it comes to sales. Start-ups don’t have the luxury to find out 6 months down the road that they took the wrong path to success. Following the straightest and fastest path to the cash separates the successful start-ups from the failures.

At Hireology I hired Kopp Consulting and their Door Opener Service. This is a company known for “getting in the door” by utilizing experienced business developers who knew how to open relationships with high-level executives. It helped us to close a number of high-profile clients in a new market we were entering.


Back to Basics for Business Success - written on chalkboard

As we role out a new month/quarter/year it’s important to think back to what has gotten you to this point.  What has made you successful?  What has worked in the past?  Below is a list of 7 basic but key areas that B2B startups need to keep always keep focus on.

1. It’s still a numbers game

  • The more prospecting calls you make, the more meetings you set, the more deals you close, and the more money you make

2. Measure everything

  • Visibility and transparency – every team member should know where they stand at all times
  • The only way to improve is to set aggressive goals, measure progress and strive to hit them

3. Battle to win customers – battle just as hard to keep them

  • We all know how hard it is to win a customer -are we then putting just as much focus into keeping them happy?
  • Is your Account Management or Customer Success process as dialed as your customer acquisition process?
  • Getting a yes is just the beginning – make your recurring revenue predictable

4. Showcase your top performer

  • As a sales leader it’s critical to have the top performer that all other team members try to emulate
  • Benchmark all other sales people against this persons performance
  • Give the top performer time to address the team and review deal cycles with them

5. Always be prospecting

  • I’ve mentioned in other blogs about separating the appointment setting role (BDR/SDR/SDM) with the deal closers (AE’s) – AE’s still need to prospect – they need to work just as hard as their inside rep to create new opportunities
  • Keep a close eye on your close-able pipeline for each AE – it always happens that when they have a lot of deals in process they focus less on prospecting

6. Effort in – Production out 

  • Put in the time and effort – results will follow
  • Determination, focus and effort can sometimes compensate heavily for skill and effectiveness

7. Follow your sales process

  • Follow the sales process you have created
  • If you don’t have a defined sales process – create one – map out successful deals – what happened and why – learn from every win and every loss




Many entrepreneurs don’t have a strong sales background and the current endeavor is often times their initial venture into a sales environment.

I highly recommend that startup organizations develop a structured sales process as early as possible.  Building out this defined methodology has a number of benefits:

  • Consistency – Each person in the organization follows the same approach.
  • Deal Strategy – Reviewing why you won or lost opportunities is critical.  With a process in place you can dissect what happened and why.
  • Limited Resources – Make the process as effective as possible and spend the majority of your time on moving qualified opportunities forward.
  • Training/On-boarding – If it’s documented, you can coach to it.  It’ll speed up the ramp time and improve effectiveness early on.

The sales process doesn’t need to be extremely complex – It just needs to followed and communicated well.

Here is the sales process we follow at Hireology:

Stage 1 – Lead Generation and Demo Scheduling
Stage 2 – Discovery
Stage 3 – Demo/Present
Stage 4 – Negotiation and Follow-Up
Stage 5 – Close and Implementation
Stage 6 – Strengthen and Grow Relationship

I include the following sections/information in each phase:

  • Stage Best Practices
  • Stage Pitfalls
  • Critical Tasks and Activities to Complete
  • Expected Outcome or Goal of the Stage

Here are some best practices to follow when building out a sales process for your startup:

  • Limit the process to no more than 6 stages
  • Clearly define each stage and who in the organization owns each stage
  • Review and analyze the process after you close or lose an opportunity
  • Don’t hesitate to make enhancements as you go – this isn’t a one shot deal
  • Communicate it to everyone that touches the sales organization
  • Make it fun/light – It’s super cheesy but we call our sales process the “treasure map” – if our team follows this process it will lead them to the commissionable treasure!


I learned everything I know on sales process from the folks at Impact Performance Group – check em out here

Also, Mark Suster from Upfront Ventures wrote a great series of posts on why your startup needs a sales methodology – first post is here



Turnover Sucks. This ebook will help.

Wondering why your sales turnover is going through the roof? Stop chasing your sales employees away and download this guide full of answers to your biggest sales turnover problems.

Inside this ebook you’ll find:

  • A comprehensive approach to understanding your turnover problems
  • In-depth explanations of turnover-reducing tips
  • Effective preventative measures


 – Click HERE to download –


Navigating the hardest hire you will make – your first salesperson


So you’re ready to hire the first sales person for your startup.  Two questions that you will inevitably ask yourself:

1. )  Why is hiring salespeople so difficult?

2. )  How do we pick the right salesperson?

Let’s dive into both:


1.)  Hiring salespeople is hard for a few reasons:

  • Even mediocre salespeople are really good at selling themselves.
  • Salespeople are a product of their environment.  Just because they were effective at selling software for X company with all of the resources that X company provided, doesn’t mean they will be effective in your startup environment.
  • Great salespeople are always in demand.
  • Great salespeople that are making good money have a really hard time leaving those jobs.


2.)  Steps to follow to ensure you are hiring the right salesperson:

  • Sell the opportunity.  Make sure that you are selling your startups vision and long term potential in every conversation.  They are not just selling you – you are also selling them on why they should take a lower salary than they could obtain elsewhere.
  • Run a structured interview/selection process that uses objective scoring in each step and don’t rely solely on your gut feeling.  (I happen to know of a great tool that can help with this….
  • Ask them to provide you with their W-2 from the last 3 years.  This will give you a good indication of how successful they were and what percentage of their compensation came from commissions.
  • Have them prepare a 90-day achievement plan.  What will they do in the first 90 days to make them successful.  This can help you gauge their motivation and excitement about the role.  It will also give you some insight on how they will approach the position.
  • Compare them to their peers.  How did they perform and stack up to the other salespeople in their past roles.
  • Run structured reference checks.  Make sure to ask past supervisors to clarify their performance and achievements.
  • Focus on their past environments.  Why were they successful in past roles?  What resources were they provided?  What were the sales cycles like?  What level decision makers where they selling to?  Get this information and compare it to what they will encounter in your environment.


One parting note:  Who should  your first sales hire be?  Should it be the eventual VP of Sales?  Or, should it be someone to cold call and find new opportunities?

At Hireology we tend to hire the person that leads the department first.  That person helps create and shape the department.  Strong ownership of that department typically follows.

This all depends on resources however.  If you can’t afford that person early on think about a performance based equity plan.



I’m lucky enough to work for an organization where the sales and marketing teams work cohesively together.  This isn’t typical, however, as most organizations constantly struggle to get sales and marketing to work better together.

I’m thankful that our marketing team:

  • Has a focus on driving our business forward
  • Does the dirty work (proposal/one page creation, lead nurturing, campaign tracking, CRM organization, trade show scheduling, etc.)
  • Pushes out gobs and gobs of great content
  • Are cheerleaders for sales, our brand and our company


Here are 5 ways that have helped our sales team and marketing team work well together:

1.) Get sales and marketing on the same page regarding lead scoring and lead qualification

  • What constitutes a good lead
  • Have a scoring system built out that both sales and marketing agree on

2.) Campaign tracking and analysis

  • Assigning marketing campaigns in your CRM to understand where the lead come from
  • You can then easily analyze data around what percentage of leads came from X campaign
  • Marketing can focus more on campaigns that yield success

3.) Create a defined lead follow-up process

4.) Bring sales and marketing together to establish buyer personas and target market messaging

  • It’s difficult for marketing to understand exactly the types of people sales is calling on

5.) Enable the environment

  • Have them periodically sit in other departments meetings to understand their focus
  • Build marketing incentive plans to reward them for increased leads
  • Set sales and marketing plans and targets together
  • Include marketing in on sales team rewards
  • Have your marketing automation tools tie directly into your CRM

LinkedIn and Hubspot (which we use for Inbound Marketing) wrote an ebook titled:

How to Create a Love Story Between Sales and Marketing

It includes some additional content on ideas to build a strong bond between your Sales and Marketing organizations.




I’m really fortunate that I heard about this book early on in my career.  I’d highly recommend this quick read if you are trying to grow a b2b startup.  Aaron Ross and Marylou Tyler provide some very strong takeaways that can help turn your company into an inside sales machine.


My 2 greatest takeaways:

1. Team Structure

2. CC2.0 Email Process


Team Structure

They focus on specialization of sales roles.  They also focus on the accountability of each team member.

The traditional sales team model typically consists of 8 to 10 sales people and a sales manager.  In this model the sales people typically run and manage the entire sales process (lead generation, cold calling, closing, ongoing account management, up-selling…)

The Predictable Revenue model focuses on small sales teams with typically a 3 people.  For example, our team is made up of these 3 roles:

  • Sales Development Manager: lead generation, list building, cold calling, targeted emailing, appointment setting
  • Account Executive: discovery/needs assessment, presenting, closing
  • Account Manager: support, cross-selling/up-selling

This also fosters a heavy amount of accountability.  There is nowhere to hide on a team of 3.  Each of these roles have very specialized responsibilities and each person is highly accountable at hitting their metrics.  The team isn’t going to be successful if all 3 team members aren’t producing.

In my opinion, this specialized team structure might not fit all organizations.  I think it works great with SaaS based platforms but might not work as effectively for Manufacturing, Pharma, CPG, Etc.


CC2.0 Email Process

This process revolves around sending a targeted email to the decision maker for your product or service, asking them who is in charge of that function (even though you probably already know the answer to it.)  For example our CC2.0 email looks something like this:


Subject: Aaron, Quick Question


Hello Aaron,

Sorry to trouble you, but can you please let me know who handles the hiring decision and hiring process at ABC Company?

Thank you,



What we have found is that if hiring (or whatever your ask is…) is someone’s responsibility they usually want to take credit for it and will reply.  Here are our typical responses:

  • “that’s my responsibility, why do you ask”
  • “I do”
  • “our current open positions are on our website”
  • “X person does”

We get astounding open rates and great response rates as well (OVER 25%!)

The benefit of starting this way is the cold call now turns into a warmer call.  The phone call is now, “Hi Aaron, I just got your email, sorry I should have put more context into my original email.  We are helping…..”

How has Predictable Revenue helped us at Hireology?  Using this model and approach helped us grow from 20 active paid subscribers on our platform to 1300 in just 24 months.  The majority of opportunities that have closed started from the simple CC2.0 process of a targeted email.